Number of times nominated: 14

Music lesson: Although he technically is a Grammy winner, Fiddy has never won for his own solo work. His sole prize (after a jaw-dropping 13 nominations in 6 years) was for "Crack a Bottle," his collaboration with Dr. Dre and Eminem, featured on the latter's "Relapse" album in 2010. But hate it or love it, the underdog's on top. Right?